The year of frozen sculptures dreaming Finlandia and lime – the ice luge – and men on stilts in dresses wearing hoops around their necks.

It was the year of free money and business plans that read like situation comedies.

And they were.

The year of billion-dollar days and SFGirl.com and climbing through the window at the Cypress Club or Jillian’s, betraying wonder.

“Gina put me on the list … Oh, wait, it might have been ….”

“It’s okay, Char – there is no list.”

Billboards north and south on Highway 101 from Novato to San Jose announcing companies without a mist of revenue. People paying one year’s rent up front in cash for the privilege of living 100 minutes from their work.

It was the year of thriving in a shared delusion, borrowed money, so much money, and faith.

There are no atheists in San Francisco: everyone believes in herself.

“If you are cautious in this market,” says the Financial Times, “you’ll miss the train.”

“It’s a new paradigm,” says the New Yorker – the New Yorker! – “and we need to abandon our natural doubts.”

Something’s new, alright. Something is abandoned.

Four or five parties a week, all South of Market – SoMa, as it’s starting to be known – two or three some nights … WildCard Wednesday and Glas Kat and Portrero Brewing … Ruby Skye and the Great American Music Hall.

After a while, it doesn’t matter where. The same people, freeloaders, the undecideds and the bored. Fucked company.

The brilliant are all still at work. This is something else at last.

What are the parties for, exactly?

“Really great networking there,” says the founder of Beenz.com, a virtual currency company … or does it sell coffee?

Parties for no reason other than to say: We’re here. No, here. Right now. In the lobby of the San Francisco Federal Reserve building rusticated with zydeco and jambalaya … Mardi Gras in March.

Charlotte raged through most of them, it felt like, and her excuse was the traffic on 280, piling up … the new HQ’s appearing on the 101 and that she’s young – twenty-five or so, let’s say – so young and fairly serious about her drugs-and-vodka rants … but also, yes, an entrepreneur of sorts, working at a dot-com in the marketing division, writing emails to people she would never meet, designing 300×250-pixel banner ads on her computer for the regional campaign.

Her company sold clothing for very thin women. She herself could not wear any of it. What do you expect from a bunch of men who dated models?

It’s a thankless life in ‘99 that’s held up by the free hors d’oeuvres … and SFBayHappyHour and the like-minded … that time Tixtogo changed its name to something else and decided to rent an airplane hangar on Treasure Island and import 3,500 people to watch racing pigs – live pigs! – and artists on the trapeze and Gold Club strippers and a go-go dancing Mayor Willie Brown, in person, live, the man.

That’s supposed to be the so-called “best party ever” of the dot-com era but she doesn’t see how that can be. Who judges these things? That blogging kid called, rather obviously, SFBoy? Who’s he?

Craigslist.com started as a website to publicize dot-com parties. That is a true story there.

It was the year of performance art – parties she knew would never happen again, until they did, again and again.

If you want to know what happens at the end of time, remember this time.

And the dead zone of every evening … the point when the over-30 – if always under 40 – co-founder mounts the floor, declines the music, waits until the lull (“Shut up!” “What up?!”) and hums, “It’s great to see you all here tonight. When I started Whizbang dot com last year I wanted to activate what I saw as some blue ocean in the market with a game-changing vision. It was a vision for ….”

Vodka! What?! Nobody remembers. Vision for real? It failed. They all failed.

Dreams die, just like people, but usually before.

The Millennium announced itself to Charlotte in two scenes.

First was that night with the cages filled with gerbil girls and that woman in a gold-threaded prom dress climbing, climbing onto the metal structure itself … and falling from the cage onto her face, dragged off, inert … and nobody stopped dancing.

Second was Guru.com.

She remembers that site because she wanted it to work. It let you set up a profile and sell your personal abilities, such as they were; “Be Your Own Boss!” like it says, your own Guru.com … but the party was just a frost on the lawn, because the people who went were actually looking for work – work! – and not enjoying the hedonic backwash of a trenchant IPO or funding round … and nothing, nothing, repels the Valley insider more completely than a person who does not propose to get rich but rather to work for a living … what a pathetic admission of defeat … even if that Valley insider is actually a deadbeat loafing sponge who has no skills herself but an ability to clean up and soft-sell a bouncer … Guru.com, that was the end.

On her way out the door, Charlotte passed two men who were saying, “What’s their margin, anyway?”

“What do you mean?”

“Are they making any money?”

“Their run rate is –”

“So they’re losing money.”

“Well, yes, of course, but –”

Oddly, she reflects, this was the first time the topic of the fundamental business comes up and there’s certainly some truth to the natural assumption that all this raving and excess and pig racing – pig racing announced by the Mayor of the Great City of San Francisco himself – and acrobats and circus freaks can’t all be going anywhere quite real. It has to end. Everybody knows it. We’ve known it since ‘98.

We know it’s going to end.

We just don’t know when.

When.

#

TheGlobe.com went public in 1998 at $9 a share. Within five minutes, it was at $97. Providing an easy way for people to launch semi-customized websites, it was exactly nine months old. The bubble began.

eBay followed and its stock price shot from $18 in September to $241 before Christmas.

“The internet,” said economics writer David Lowenstein, “had now reached the stage in which people cease to think and simply imitate each other without any regard to the underlying economics – in other words, a bubble.”

Broadcast.com provided streaming media over phone lines that turned the stream into a trickle and a wait, like a hot tub on Mars, but somehow Yahoo decided it was worth paying almost $6 billion for it, making a young man named Mark Cuban very rich indeed.

The MGM Grand hosted the biggest boondoggle of all – in Las Vegas, of course – called the iBASH 99. It cost a rumored $10 million and was supposedly staged to promote an unknown company called Pixelon that was either a criminal waste of money or a criminal plot. It was bankrupt in a year, having launched nothing.

Traffic was just unimaginable as kids drove from the city to dot-jobs up and down the path to Palo Alto.

And then it got worse.

Advertising was both symptom and cause of the boom. In 2000, 69% of all online ad dollars came from dot-coms. Of course, they advertised themselves.

So the bubble was stoked by dot-coms buying ads, creating media empires like Yahoo that bought dot-coms like Broadcast.com, driving up the value of other dot-coms and inspiring VC’s to fund companies that then, yes, bought ads from online media companies that … and so on.

There were other ideas. Free-PC.com gave away Compaq PCs. In return, its victims watched a stream of ads crawling along their (free) screens. AllAdvantage.com sent customers checks based on how many ads they watched. Its founder was a recent Stanford grad. The week the NASDAQ peaked – at around 5,000 – Credit Suisse’s oily-haired Frank Quattrone took that founder and his team by private jet to Aspen for a weekend none of them can quite recall.

In its most recent quarter, AllAdvantage.com had sold less than $9 million in ads and paid out almost as much to its ad-watching customers, many of which (it turned out) were robots. AllAdvantage.com did not know they were robots. They cashed their checks too.

And then came Super Bowl XXXIV. During the course of a strategic dialogue between the Rams and the Patriots, catalyzed by a brilliant Tom Brady, sixteen different dot-coms aired 30-second spots. Each cost about $2 million.

The most telling was the pitch for a company called IWon.com, which had the so-called business model of giving away online games and its investors’ cash in $1 million bundles.

Even as the Pats were celebrating, the NASDAQ stopped climbing. It had muscled up 5X in five years.

One year later, during Super Bowl XXXV, there were only three dot-coms showing ads. Two of them were job-hunting sites.

A research firm predicted that by 2005, the share of internet ads bought by dot-coms would plunge from 69% to 16%. The average price for online banner ads went from $50 to $5 for 1,000.

After March 10, 2000 – as Quattrone towels off after his hot tub luau in Aspen with the soon-to-be-bankrupt AllAdvantage.com team – the NASDAQ index starts falling … and falling … and after thirty sickening months is down 78%.

#

Charlotte joins the exodus. It is a relief, in fact. She abandons her lease in Petaluma in March of 2001 and drives east, by herself, to New Jersey.

There is a man involved in this decision. It takes a moment to recover from a two-year binge. Not working actually helps. Her company – that website for the minus-sized woman – just disappears. One day, the door was locked. There was a note:

“FOR LEASE”

The founders, frat brothers from San Diego, evaporate. She’d seen them nearly every day for two years; she never heard from, or of, them again. Nobody knew. Hard times are like that.

And the man involved, he had attached himself to her along the way and would not, when it came time, let go. Looking back, she sees he was obviously on one of those mental spectrums they have in the technical fields, but psychology did not help her get rid of him, nor did blunt talk and unanswered calls.

It was time to move. She liked the idea of New Jersey. It seemed somehow more adult than SoMa.

Where she ended up was sharing a third-floor one-bedroom dump in Hoboken with a girl named Lauren who wore three kinds of purple eyeshadow and worked in a bar called Lapine’s. She was a walking wreck, this Lauren.

Note: I originally published this rather bitter essay about my hilarious lack of talent as a fiction writer in Medium. I had never published in Medium before, felt it was perfect for my work, pushed play and sat back waiting for the world to change. It didn’t. Three people read it; I know this because Medium, unfortunately, counts. I offer it here because I’m confident it will be seen by more than three bots. Enjoy.

I am the worst fiction writer in the world. No, I am not making this up. I couldn’t if I wanted to — I’m incapable of making anything up.

This sad situation is not due to laziness. I put in my ten thousand hours, my workshops and night classes and day classes and drafts; my editors hired and martyred and shamed into feedback; my competitions and applications and plaintive pitch notes and paper — scaffolds and dumpsters of paper thudding onto a dozen desks in a half-dozen states, crushing haulers, filling zip drives, hurtling off into the library of forgotten words.

I do not blame a bad education. I do not blame my parents. They wanted me to be a writer; at least one of them did, at times. I can not blame a lack of confidence or dyslexia or addiction or myopia or a broken social scene or the hard and brutal scythe of luck, which seemed to like me fine. I got every break in the book, but there was a problem

That book was fiction. It was written by me. And it sucked.

I am a wonderful reader; a gifted reader. I will linger over an effect in, say, Nabokov or Ira Levin’s Stepford Wives — eclectic tastes — and think, “Wow. Look at that.” I’ll read the Golden Age mysteries of Christie or Carr, the relentless final chapter of Ulysses, the invention of The Island of Doctor Moreau — and go blank in the face, flooded up to my eyes with blue envy.

Wow. Look at that. I can do it. I can do it, too.

There was never a time when I did not want to be a novelist, a playwrite, a hipster L.A. showrunner with a staff of lesser writers, chunking out a storyline, sawing out a plot. Desire, I had. Tenacity — too much. Solitude — oh, boy. But there was a problem; there was always a problem.

I was so bad at fiction I did not know that I was bad.

In fact, I see now that my own epic optimism about my fiction-writing skills was itself proof that they didn’t exist. It is a well-attested psychological phenomenon, one with a name. I discovered it too late to make a difference, but I share it now so you can quit while you are young. It is called the Dunning-Kruger Effect, and it describes a howlingly tragic phenomenon wherein people who suck at something don’t know they suck because their ownsuckiness itself makes them unable to see their own suckitude.

Wow. Talk about irony. A disease whose symptom is its own invisibility. Don’t linger here. It’s actually a very, very funny phenomenon unless you happened to discover, about two months ago, that it took a whole honking hunk of your so-called life out behind a shed somewhere and shot it.

Self-knowledge is wonderful, but not when it comes too late. Neither Dunning nor Kruger and a busload of their Cornell University grad students will never be able to give me back those years of my life, my glorious time, when I should have been whittling myself into a conscious contributor, a professional fellow in a black suit and Tesla, a man with some heft in the world — a dry wit who does something, adds a certain personal competence to our collective human project, draws an honest breath — and not what I am: a delusional non-novelist and non-screenwriter, some schmuck with a Lenovo.

I am not alone. You know this: I am not alone. The world is filling up with atrocious artistic abortions and witless videos and literary loogies that should be lying on a slab somewhere. But most of these things are committed by kids, twentysomethings, mammals in the midst of growing up. “There is a kind of lambent tragedy that occurs in too many young men,” said Edmund Wilson, “who mistake a youthful passion poured out in poetry for a real call to the art.” That’s me.

As I say, I’m not alone, but I am willing to bet that in the annals of failure I rank pretty well. How can I say this? Imagine a ratio — we’ll call it the Rat Ratio — that divides the sum total of all signals of success (however tiny) by the total amount of honest effort put into that success. Nobody — not Charles Dickens, not Stephen King — makes it all the way to one. That would mean every tap-tap of effort yield a tap-tap of success. No life I know goes like that. Everyone hits a pocket of air. Energetic bad writers have low numbers, sometimes very low. My ratio is lower than that. It is zero.

What? It is my pained duty to report that, over two decades of trying and trying again, churning out (at last count) a dozen unpublished novels, uncounted poems and short stories, at least two dozen crapulous screenplays and pilots and spec episodes for television programs now dead or dying — during year upon year of studious, near-psychotic endeavour — I never received a single word of encouragement. Not one.

Zero divided by a google is still zero. That’s the sum total of my success as a novelist, short story writer, screenwriter and television staff member. Zero. Tell me now that I am flattering myself, that my failure is not as impressive as I claim. No, I am not; and yes, yes, it is.

I am rock-solid in this statement, at least: I am utterly, entirely, completely, totally and convincingly without a shred of talent as a storyteller.

The Problem of Storytelling

That’s the problem, of course: storytelling. Making things up. Putting one made-up thing after another in a way that creates a sense of wonder, a logical flow. Don’t tell me about story structure: I know the Hero’s Journey. I know about the rise and fall of action at the end of an act. I know about acts. I watched the hundred best movies of all time, plotted them down to the minute, distilled their essence into a template, pressure-tested the template against new hits and wrote my own version of the Perfect Screenplay.

But there was only one problem. I wrote it. And it sucked.

“Every suburban sewing circle has one,” says William Goldman — who, unlike me, is a natural storyteller — “someone who can tell a story around a table and keep everyone waiting to see how it turns out.” He is certainly right about this: it’s not a rare gift. My wife can tell stories with a rising swell and moments of hilarity and suspense. So could a guy named Aki in the ad agency where I worked measuring the impact of campaigns. Great stories, riveting works. They do not call themselves writers. I do. The most common reaction to a story I tell out in the plain air is a desperate silence and, suddenly, “What?!”

I’m confusing. I confuse myself. I don’t have a cumulative style — you know, how a story unreels like a soft desert sunrise, slowly at first but with light dabbed on at intervals until the scene is ablaze . . . and then they appear, a hat and a leathery pinpoint, shots, a violent chase . . . changes in the texture of sand as the body falls and it turns out, unbelievably, to be . . . .

Don’t ask me. I’m the last guy who knows who should turn up in a story and where to keep the beat beating. I can’t do suspense. I can’t do drama, or comic narrative, or action-adventure or horror or anything at all. How do I know this? Because I’ve tried them, tried them all. And I suck.

“Keep trying,” they told me, all my pained readers. “Nobody gets it right at first.”

And: “Why don’t you put it away for a while and come back to it?” (Which is like locking a crazy cat up in a closet, hoping to improve its personality.)

And, later: “Maybe you should try a different type of writing. Thrillers are really big now.”

Thrillers are big. So is horror and suspense and literature and romance and fantasy and basically anything that has the absolute non-negotiable element of everything that is big then or now or ever until time stops and we all go the way of all life: the one true thing. A riveting story. Told by somebody who knows how to tell a story.

Talent exists, people. It is not a game. Some people have it, and some people don’t.

Don’t encourage assholes like me. Yes, a craft takes time, and it is a crime to step too hard on the young. But a forty-five year old schlemiel injecting his fifth semi-autobiographical piece of rancid vomit from a word processor into your life must be kindly, but decisively, stopped. If kindness doesn’t work, take a firmer stand. Do not relent. Do not say “Time takes time,” and, “It’s just one agent’s opinion,” and, “The market’s weird right now.”

The market’s always weird. Time takes time but does not make miracles. People who suck long enough and hard enough at something will always, always suck. It is the law of fiction physics: there is no path from nowhere to good. There is no water rising from an empty well. It just sits there, like your relatives, staring at you single-eyed until you wise up someday and leave.

We are not happy, we people with my kind of dream. I’m not exactly sure why we go on. At first it’s a reasonable sense we can get better, or are overlooked. With enough rejection, we become angry. A mature reaction to non-stop failure is to try a different approach, find another dream. Right? But too many of us have a bulldog tendency, a fighting spirit that is wonderful in war and if we’re protecting an injury or a child or a venture capital-backed start-up ahead of its time.

In a person who just plain can’t do something, tenacity is not a virtue. It is a vice.

Obvious Awfulness of the Roller Coaster

At this point, you’re wondering what I actually wrote not at all. You don’t care. Nobody cares or ever did but I have a certain pride now — with the benefit of a horrible hindsight — in the obvious awfulness of my work, my ideas. How could I have thought they were contenders? How could I have embarrassed myself like that?

I once wrote a screenplay called Roller Coaster. Stay with me. We’re in a theme park kind of like DisneyWorld. A bunch of randoms get onto a roller coaster. Ten minutes in — yes, I know about the Inciting Incident; I took Story Structure from Robert McKee himself, bros — ten minutes in, there’s a problem. Suspicious characters appear and — BAM! — terrorists have taken control of the park. They occupy the control room . . . and decide to keep the roller coaster going, over and over again, without stopping, until their evil demands are met. Of course, there’s an intrepid undercover cop with a troubled past on the roller coaster as it hurtles around and around (and around and around) . . . and, somehow, he saves everyone without getting sick on the camera.

Genius? Nobody bought that one. I showed it to a friend of mine from college who literally acquired screenplays for a major studio — see, I did not have bad luck in life — and he said, “Marty, I’d like to help you, but this is not a screenplay. I don’t know what it is, exactly. Try again.”

Try again. I wrote a kind of alternative-universe script in which women are on top and men are treated like objects, a super-sexist upside-down world, and I called it Living Doll. It was set in the region of advertising, and I had great fun making the women fat and old and sloppy and the men obsessed with aging and their looks and babies and . . . there’s a scrappy (boy) secretary who’s got a great idea and his (woman) boss takes credit for it and . . . well, if you’re thinking, “Hello, Working Girl!” here, you’re more than half right. I borrowed plots because I could not think of them myself.

My studio friend didn’t call me back on that one. Now that I think about it, I haven’t talked to him since. Try again. Having an analytical mind, I came up with explanations for my failures, like some drunk trying to figure out why he keeps going waking up in handcuffs. I was missing my strengths. What was needed was a more ambitious approach.

So I settled in and over two long years that stretched back into the origin of the universe and outward to its end — or so it seemed — I created a 120,000 word novel about Cornelius Vanderbilt and Jay Gould, late 19th century railroad barrons, set in 1876 in that greatest of fictional cities, old-time New York. Sounds interesting, right? I read dozens of books about the period, including an encyclopedic tourist guidebook published in 1872 called The Sights and Sounds of New York — a riveting work, actually, showing how little the place has changed over the years — drew maps, dove into the archives of the New York Times (which was a right-wing rag then) without coming up for weeks on end . . . accumulated a meticulous record of clothing, streetcars, etiquette, food (the “Hamburg steak” was a new meme), commute times (averaging one hour, as now), policing, Wall Street . . . and wrote a story.

By this time, I had a literary agent; a respected young man with good taste. (He did not sign me for my fiction, of course; I also wrote non-fiction that was, apparently, better.) He read it and offered advice. I rewrote it. He read it and offered more advice. I rewrote it again.

He called me. This call, I will never forget. I had broken my foot in the Uppercut Boxing Gym on New Year’s Eve and was staring out on my city of exile, Minneapolis, where I’d retreated (with my sainted wife, a Minnesotan) to work in advertising analytics and wonder why my fiction-writing dream wasn’t working for me yet . . . .

“Marty,” he said, “I have to be honest.”

“Mmm.”

“Why don’t you put this aside. It’s not happening. You tried three times and it’s not –“

“But, but –“

“Or you could hire someone to help you, really get in there, work with the — you know — the words.”

“You mean, an editor? I thought you –“

“No, a coach, a — someone to really get in there and –“

“You mean, a writer? You want me to hire a writer to write my book?”

You can imagine that — to a writer — the advice to hire a writer to write the writing comes as rather a splash of cold juice.

Agents have my respect. They’re dealing with the most immature people in the world at their most vulnerable, on the topic about which they are blind and defensive by nature. To say I sobbed for weeks over this conversation would be to state the obvious, and all that poor kid did was tell me the truth.

My novel sucked. It blew chunks. It was called The Strategem and somebody should have put it in a leaded sink and burned it, scrubbing out the residue with bleach.

Try again. So perhaps historical fiction was not my forte. Certainly, there are easier forms. Write what you read. More terrible advice from the orphan train of writers’ workshops. Great readers do not make great writers; great readers make great book reviewers.

Minnesota Mediocre

Minneapolis has a lot of faults but one thing it does really well is nurture and encourage bad art. It has a thriving community called The Loft that is like a hatchery for terrible poetry and execrable prose. Hot off my Strategem stink bomb, I decided what I needed was a supportive artistic community, one with a lively give-and-take of encouragement and praise, a prop in the midst of my (temporary) disappointments. You see where this is going. I take a class. Two volunteers for next week? — I’m in! I write a story called “The Ranch” based on a trip I took with my long-suffering to a spa called Canyon Ranch in the Berkshire Mountains, a binge I felt I needed to help me get over the failure of my — at this point, I think it was still the historical thing — and it was the worst week of my life. Add to the post-operative environment and food that was all but literally twigs, bark and berries — the tick-tick of ruinous bills racking up by the moment — add to that my wife’s gentle suggestion that we take, um, a marriage workshop, you know, while we’re here . . .

It was okay. She cleared the air. I took it manfully. Once they released us, it occurred to me that Canyon Ranch was a great setting for a story about mind games, out-of-control therapists trying weird experiments on touchy couples drained of hope. That was “The Ranch.” I emailed it to the class with an ominous pride.

“I don’t get it,” they said, as one voice. “What’s going on here?”

“You know,” said the teacher, a local small-press novelist, “you might want to start over with this one.”

“What do you mean?” I asked.

“Start fresh. Rethink the concept.”

“You mean, throw it away?”

Throw it away. Burn it. Flush it. Rid the biosphere of this fictional homunculus that has wasted our time and yours and subtracted minutes from the people for no reason but the gratification of some screwy ache on the part of a now middle-aged man to chase a dream like a beloved Bernese mountain dog across a glorious field of high wheat that’s on fire — the field is on fire — and nobody’s getting out of this thing alive.

I quit the class. I should have stayed. I’m a good reader, as I’ve said, and my comments on other people’s stuff can be useful. I’ll never write a good story, but I know one when I see it. When the Greek philosopher Thales was asked what was difficult he said, “To know yourself.” And what was easy? “To advise another.”

So it goes. I was not done yet; not quite yet. The past three years I committed three complete novel-length objects, and it will tell you just how near death the enterprise had become by this late date when I admit that two of these objects were cat mysteries. Say what? You read that right: cat mysteries. Mysteries featuring felines as intrepid crime-solvers. Not for kids: for adults.

It’s a real genre, one I like. The first four novels by the late Lilian Jackson Braun are favorites. Don’t knock it till you’ve tried it, girls.

Cat mystery #1 was awful, so ghastly no one but me (and my cat) will ever see it, but the second wasn’t worse. I called it I, Cat! with a flourish of neo-noir silliness, actually hired an editor to help me out, sent it off to the boy agent in New York with head high.

“It just doesn’t work,” he wrote me in an email. “Let’s talk about it.”

We didn’t. I let him go and went on a religious retreat and prayed for an answer, and I’m thinking there is some divine art at work in the answer I got as though spoken to my soul itself.

The mighty AdExchanger just published its annual list of most-read columns, and I’m proud to have written 3 of them — that’s 30% of the entire cadre, friends. They call them “opinions” but really, I just write the truth. If you’d like to enjoy them again (and again), the winners (along with the great Tilde Herrera’s precis) were:

Google sent shockwaves through the industry in late April when it announced that it would restrict buyers’ use of the DoubleClick ID. Kihn puts the controversial move under the glass and predicts the likely winners and losers (sorry, independent MTA vendors).

People have long griped about the digital advertising industry’s obsession with the latest shiny object. The newest shiny acronym to hit is the CDP (customer data platform). Kihn breaks down the pros and cons of the tech that aspires to bridge marketers’ siloed data and systems.

This story ran in the mighty AdExchanger last week attributed to “an external contributor who prefers not to be identified.” I thought more people would suspect me, but apparently they don’t read the Gartner blog network.

Suddenly, last summer, Google announced it was erasing the DoubleClick name from its product portfolio. So ends 23 years of ad tech myth and legend that coincides with the ad-supported internet itself.

DoubleClick rode the dot-com boom to heights of overcapitalization and came crashing down with everyone else in 2000. It created New York’s Silicon Alley, had outrageous parties and heavenly bills and saw just about every future ad tech luminary pass through its cult.

The iconic sign that loomed over Broadway and 22nd Street during the days of the boom defined an era:

“DOUBLECLICK WELCOMES YOU TO SILICON ALLEY”

It was an ad network and ad server before anyone knew what those were. It provided a sales team and infrastructure for advertisers to buy ads from multiple publishers in a single location, target them using criteria such as location or time of day, insert them into web pages automatically and get reports. It has quietly dominated ad serving since it started and thrived as a brand since being acquired by Google in 2007.

Success is obvious in reverse. But in the summer of 1995, two engineers named Kevin “KO” O’Connor and Dwight Merriman were sitting in O’Connor’s 2,500-square-foot basement in Alpharetta, Ga., looking for something to do. They had cashed out a networking startup in Ohio and moved south to raise families.

Kevin O’Connor, co-founder: Dwight and I came up with hundreds of ideas and narrowed them down. The original concept was a network of publications, like a cable subscription model. Then Dwight looked at how media monetizes and said advertising could be bigger. We flipped the idea into a network of advertisers.

David Gwozdz, sales director: Kevin called me and said, “I understand you’re a good ad sales guy.” I went over to his house to tell him no thanks – and ended up taking the job. Kevin met my wife, and the first thing he said was, “I’m going to make your life hell.” We worked seven days a week, morning to night.

O’Connor: Dwight was coding, and I was learning about advertising and direct marketing from textbooks. I was going to the library reading Ad Age and Adweek to see if we had any competitors.

Gwozdz: At that time, the ad server was an ISDN line and a 486 PC on Dwight’s desk with the cover off, because it kept overheating.

O’Connor: I read in an article that an agency called Poppe Tyson was doing the same thing. I thought, “Holy crap!” and called a guy there named Dave Carlick.

David Carlick, EVP, Poppe Tyson: Our interactive group was called DoubleClick. The name was invented by [Poppe Tyson CEO] Fergus O’Daly. It wasn’t a good name. It’s an old Apple term. A click on a URL is a single click, not a double click.

O’Connor: It turned out they didn’t have any tech yet. It was the classic, “Let’s launch an idea and see how the market reacts.” We were just completing the product, and they had a team of four selling ads. We decided we should work together.

Carlick: There was a long discussion about whether it should be based in New York or Silicon Valley. We decided on New York and started the whole Silicon Alley thing. The story is that when Kevin and his wife saw the tiny apartment they would have to live in, they cried.

After a tentative start, the company started to, um, click but banged into sales teams from websites like Netscape and Excite, which were Poppe Tyson’s major clients. So Fergus O’Daly decided to spin off DoubleClick into a separate subsidiary with Kevin O’Connor as CEO.

O’Connor: We were 50% owned by an ad agency. No one liked that. We tried to sell the company to someone else. There was a deal with Yahoo back in 1996 – we wanted $100 million and they offered $95 million. They wouldn’t budge.

Kevin Ryan, CFO (later CEO): I was thinking about starting an ad network, so I met with Kevin and Dwight. I thought they were very good – they had a six-month head start. So I became employee No. 12. We grew very quickly. Four years later, we had 2,000 employees in 25 countries.

Gwozdz: I was still in Atlanta, in a little office usually by myself. I remember I went to a sales meeting in Colorado Springs, and there were 200 people in the room. I didn’t understand how big this was getting.

O’Connor: Everything started to go through the roof – a lot of revenue, with hefty margins. We needed capital. The mantra was “get big fast.”

Gwozdz: We started picking up pub after pub. We were an upstart with really good tech no one else had. We could target by location, time of day, exclusion. People would light up. They loved the reporting.

Bill Wise, director, financial planning (later VP/GM): KO would get up in these meetings and he was so aggressive – we loved it. He said, “We are the company that is changing advertising and media. We won’t stop until we have world domination.” It wasn’t a job, it was a cult – a feel-good cult.

DoubleClick went public in 1998 on the Nasdaq exchange under the ticker symbol DCLK. It was the beginning of the bubble’s last bleat. The Nasdaq rose 86% in 1999. It soared 5x from 1,000 to 5,000 in the five years before 2000. There were 15-20 dot-com parties every week in San Francisco. About 70% of digital ad dollars came from VC-funded dot-coms. Of course, few people suspected what was coming. They were just trying to find a place to sit.

Wise: There was a temp who was working under [VP of sales] Wenda Millard – a great kid – he was sitting in the hallway. One day somebody put a “Kids in the Hall” poster up behind his desk and crossed out the “s.” He was known as the “Kid in the Hall.”

Brad Bender, director of product management (later VP): They put me where they’d moved a copier out. It was the world’s smallest desk. I was the “Kid in the Hall.” The executive team was right around the corner from me. I remember Kevin O’Connor came by with clients and said, “Look, we’re growing so fast, we even have a ‘Kid in the Hall.’”

Wise: Eventually we maxed out the space and threatened Manhattan that we were going to move to Jersey City. They ended up giving us tons of tax credits to keep us, since we were the founders of Silicon Alley. We built out the space on 33rd Street and 10th Avenue.

Scott Knoll, director of business development (later VP/GM): 33rd Street was a brand-new building. It had a climbing wall, a multimillion-dollar basketball court. We had to build a special platform to muffle the noise for the tenant under us. It was spectacular. There was a view of the Hudson River. Bleachers. Fiberglass backboards, a scoreboard and lighting.

Wise: DoubleClick had the best parties. KO was at sales conferences playing guts and taking stock options as currency.

Ryan: We went all-out at Halloween. Everyone came to the office in costume. One year I showed up as a mummy. I had trouble getting a taxi and I couldn’t get into the building. I had to remind the manager that he knew me. Then 200 of us marched up Fifth Avenue at 10 a.m. in our costumes.

Then the company got a real scare. It decided to merge with Abacus in 1999 for $1.7 billion. Abacus was a consumer data co-op that tracked the catalog buying habits of most US households. Trouble was, it used personally identifiable information, which DoubleClick proposed to map to its (anonymous) cookies.

O’Connor: Abacus was a great company that had a tremendous amount of offline purchase data. That acquisition was about ways to combine offline and online consumer purchase data. We weren’t wrong about it. But we came up against privacy concerns.

Wise: USA Today published a story that DoubleClick was going to try to marry online and offline data. It got picked up by other publications and got a lot of attention.

Knoll: Abacus was frustrating. It was a situation where the influence of media was major but they didn’t have the story right. Nothing had actually been done yet.

Wise: KO took the fall, as a great leader does. He cared more about the company than his own legacy. It was sad how it went down.

O’Connor: I can’t say Abacus was overblown. It is what it is. People were afraid. I left [in July 2000] because I couldn’t see a path to where I could enjoy my job. I’m a product guy and an engineer. I like building things. I was a reluctant CEO. In the end my job was just dealing with politicians, the media and lawyers. I wasn’t good at it. I was burned out. Fortunately, Kevin Ryan loved dealing with those folks, so he stepped up from president to CEO.

What went up came down. In the 30 months after the market peaked on March 10, 2000, the Nasdaq fell 78%. Between 2000 and 2001, the Super Bowl went from airing 16 dot-com spots to three, two of which were job-hunting sites. By one account, CPMs for banner ads fell from $50 to $5. More people were leaving the Bay Area in panic than arriving with hope in their hearts.

Ryan: Most of our publisher clients went bankrupt. It was Pets.com times 100. Those were our clients. We did seven rounds of layoffs and went from 2,000 to 1,000 people. We turned over the entire management team. A lot of them couldn’t do the sixth round and still feel good about it.

Bender: It was a challenging time. It wasn’t clear when we were going to be done with the cuts. A lot of people I valued as colleagues and friends weren’t around after that period. But it was a healthy retrenchment.

Ryan: We lost 30% of revenue but eliminated 50% of cost. So by 2004-05, we were actually profitable.

Ari Paparo, VP, rich media: When I joined [in 2004], there was no structured onboarding. My boss quit on my third day. The layoffs were done, but it was just a crappy company. It was dysfunctional, engineering products that were incredibly bad.

Ryan: In 2005, our valuation was very low, just like everyone. The board felt we were undervalued, so they hired Lazard and interviewed 50 buyers.

Paparo: The company announced publicly it was going to look at strategic alternatives nine or 10 months before [SF-based private equity firm] Hellman & Friedman closed. Even Google bid a fraction of what they later paid.

O’Connor: Google’s perception was that we were a sales company. They thought tech could only be built in Silicon Valley. They were wrong – as they realized later.

Ryan: DoubleClick sold at a 50% premium to the stock price. Kevin and Dwight and I didn’t think that was a good price. We thought the board might be wrong. They didn’t know that the ad volumes had already turned up.

Paparo: David Rosenblatt became CEO. He quickly made some hard decisions. He sold off the mail division, closed Abacus in Europe and sold Abacus, sold marketing automation. The product team was a lean mean machine. There was accountability and process.

Bender: Hellman & Friedman came in and clarified the lines for each of the component parts. They focused on the ad tech use case. They were clear.

Gone was the 33rd Street pleasure palace, aka “Click City,” replaced by a less lavish space on Eighth Avenue. Abacus was sold to Epsilon. DoubleClick was shopped and Google jumped. Its expansion from search into display was not beloved by all. Microsoft objected before the Senate Subcommittee on Antitrust that “this acquisition would give a single firm exclusive control over the largest database of information on individual online behavior the world has ever known.”

But the deal closed in April 2007, with Google paying $3.1 billion in cash. By any measure, it was a very smart move, expanding Google’s power in programmatic advertising. It also domesticated the demon.

Paparo: DoubleClick was on the eighth floor of the Eighth Avenue location, and Google was coincidentally in the same building on the fourth floor. When the acquisition happened, the first thing they did was wheel in truckloads of snacks. That was their first impact.

Bender: Google operates like a small company, even though it isn’t a small company.

Paparo: Everything changed under Google. It had a big impact on the company’s culture. It was more engineering-driven but more whimsical. Less business-oriented. Google cut a quarter to a third of the jobs, and they were unwilling to allow legacy tech to survive.

Bender: I brought a couple ideas to strategic planning to fund, including yield management and the ad exchange. The exchange was ultimately brought to fruition by Scott Spencer and Michael Rubenstein and became AdX.

Paparo: There were no crazy parties. No shenanigans. People had kids. The expense accounts were not like they were before the crash. But our class made a lot more money. The early guys had more fun, but they ended up with stock that was worthless.

O’Connor: It is viewed as one of the most successful M&A deals ever. I’m happy it lasted so long and continues today under the Google brand.

Bender: It’s bittersweet for me to say goodbye to the DoubleClick name after 20 years. But it delivered on the mission of becoming the operating system for advertising.

Last month, I put this article up on LinkedIn Pulse and went on with my day. The response was extraordinary — far more energetic than I expected. Over 10,000 views, 1,000+ likes, 190 shares and 189 comments (and counting). The comments were particularly fulsome and encouraged me to be more honest in the future. For now, in case you missed it:

Monday — on what would have been my five-year anniversary at Gartner — I left to join Dentsu Aegis Network. It was a good span at a well-run company doing God’s (technical) work. It was simply time.

When I was a management consultant, I couldn’t describe what I did. Not to my parents, not to strangers. Not in a way that convinced them I had a real occupation, and maybe I didn’t.

So most of my inquiries took the form of: “How can I measure the impact of my ad campaigns?” … or, “How do I organize my campaign data for targeting and measurement?”

Those were the real questions. See what I mean: Not unique. Any marketer could (should) ask them.

The trouble is, the way they are originally phrased in the meeting invitation makes them sound like some fragment of the Dead Sea Scrolls. “We’re in the process of spinning up a 360 view of the customer and we need to find a universal ID we can map to our CRM and MCCM but the customer files are all sitting in the data warehouse we think …”

Real question: “How do I organize my customer data?”

There is no 360 view of the customer. Give it up. Marketing profiles are by nature incomplete. They should be. We’re not building an encyclopedia. If we did, we wouldn’t have time to read it. We need only one piece of information: the right one.

She really wants a pair of red shoes now. She’s not price sensitive.

He secretly wants to test drive that Tesla but has to convince his boyfriend it’s safe.

The only thing he really loves are Bernese mountain dogs.

These are far from 360 but are perfect for marketing.

Most clients of analyst firms do not use the service enough. They mistake it for a Delphic Oracle that is sometimes wrong, rather than a research tap that is often right. Ask a question in advance. Most analysts — like me — spend time preparing for the call. This is called research-on-demand.

Sometimes I think research is my only real talent. And then I remember that I am also a dog trainer. And then — then I realize I am very bad at that.

Vendors sometimes believe analyst firms do P.R. for them or they can pay their way onto a Wave or Magic Quadrant. I have been deep inside the machine, my friends. This belief is not true.

There’s not even much of a benefit to being a client, unless you want to use the service as a service, like other clients. It can help you craft your story, improve your pitch, not sound like everyone else; anticipate end user needs, murmurs in the market; help you emerge from the bubble wrap of hermetic V.C.-and-conference-speak, which seems — from what I can see — to be much better at building brilliant solutions to invisible problems than at finding problems that need to be solved.

Most marketers are not advanced. The real disease we all have is an inability to admit we have no idea what real gangstas are talking about.

“I just wish I were more technical,” a very well-regarded ad tech analyst told me recently.

“We all do,” I said. And it’s true.

Our agenda this year should be to admit what we don’t know, not promote what we do. Don’t nod along if the point is obscure. The talker is faking it anyway. Nobody knows the difference between A.I. and machine learning or why they’re conflated or how to get to a local maxima or why you need XG Boost today when a simple gradient descent algorithm worked yesterday … it’s okay.

If you knew it all you’d be dead, right? There is perfect knowledge in silence. It takes a lifetime to be a good mystic too.

Most vendor briefings are just not very good. They are too long. They wander from the point. From too many it is impossible — and I say this as an intelligent insider who knows a thing or two about your market — completely impossible to say what the product does, exactly.

You don’t do everything. You don’t sell to everyone. Pick your fight. The best predictor I know of a doomed start-up is not a weak board or a psychotic founder, it is a polished pitch deck.

The best start-ups I’ve met are modest and clear, friendly and fairly honest. They do not spend five slides telling me that Millennials crave experience and mobile is the new Web. They do not say the DMP or email or apps are dead. They do not say anything is dead or that everyone else “just doesn’t get it.”

Above all, they do not say they have no competitors.

Think about it, people. Who has no competitors? Who? I’ll tell you. People who are in a market that doesn’t exist. Delusionals. Hallucinators.

Use 12 slides. Don’t have any set-up. Tell me what you do. Name your three competitors. Say what about your tech is proprietary, original, or interesting. Explain the things you’re going to improve. Describe your funding. I liked a demo, if there’s time.

Maybe once or twice a year, I encountered a new company that seemed to me like a winner. I’m trying to think why. They had very little spin and a lot of technical detail, but not as hype. They seemed to be engineers talking to a blogger rather than sales people who had read some white papers. They were somewhat awkward, informal. And their products all emerged from a technical discovery – a thesis, an experimental approach, an application of some new platform to an persistent problem.

A problem like: “How do I reactivate dormant customers?” or “How can I link records faster?” or “What is the real LTV?”

And they all wanted to learn. What have you heard? Is this thing needed? Are we lost in emotion?

Good products take off fast. They surprise their creators with momentum.

If I can indulge in a reflection, I also learned some things about myself. It is important to manage burnout, whatever your age. Working life is a marathon. I’m not talking about getting enough sleep or eating right or exercising; you know that. I mean in the long run, over years, managing a build-up of stress that tears you down from the inside until — one day — you realize you simply can not make another phone call, write another document.

The only way to recover from this situation is to take time off work. As much time as you can afford.

But don’t let yourself get there. You can avoid it. Take vacations. Cultivate a hobby that has nothing to do with your work. Get a Bernese mountain dog. Get married. Hike alone.

Don’t fight fear. Live bravely. Smile more. What we forget about the Hero’s Journey is that it does not change the world. That is not the point.

I am an author, digital marketer, ad agency alum, former management consultant, and programmatic advertising pundit. I was born in Zambia and moved too often, ending up in Michigan. I consider myself to be a Midwestern Gotham-manque. After college, I stormed NYC and was a fact-checker at Spy, reporter for Forbes, feature writer for pubs like New York, GQ and the New York Times.

My best-known writing job was as Head Writer for a program called Pop-Up Video on MTV Networks. We were nominated for a Daytime Emmy, and my mother has a picture of me and then-Mayor Rudy Giuliani. His tan is smoother.

After business school, I became a management consultant and published an irreverent memoir of that experience called House of Lies. This book later formed the basis of a Showtime series of the same name starring Don Cheadle as a highly stylized version of myself named Marty Kaan. It ran from 2012-2016.

You can see me on the right side of the stage here with the stars and producers of the show:

My most recent memoir is Bad Dog (A Love Story). Altogether less snarky and more emotionally satisfying — at least, to me — this book told the story of my beloved Bernese mountain dog, Hola, who taught me how to be a sober man by training me for our Canine Good Citizen certification. It too was in development (at NBC) for a time.

Professionally, I’ve worked on the analytics and measurement side of the digital advertising business since 2004, at agencies in NYC and Minneapolis. Currently, I’m a Research V.P. at Gartner, covering advertising technology and digital marketing analytics.

Much of my professional writing, which has won internal prizes (twice), sits behind the Gartner firewall. I’m also one of the firm’s most-read bloggers, and I contribute pieces from time to time to various worthy sites like the mighty AdExchanger.

My passions in life are modern ballet, particularly NYC Ballet and this person, and Bernese mountain dogs. I live in Katonah, NY with my wife, the singer-songwriter Julia Douglass, our BMD Jordan, and this rather dominating personality, Jerry: